Efficient Regiospecific Conjugated Ring Fusion in N-Confused Porphyrin

被引：26

作者：

Chmielewski, Piotr J. ^{[1
]}

Maciolek, Justyna ^{[1
]}

Szterenberg, Ludmila ^{[1
]}

机构：

[1] Univ Wroclaw, Dept Chem, PL-50383 Wroclaw, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 23期

关键词：

Porphyrinoids; Aromaticity; Macrocycles; Fused ring systems; EFFECTIVE CORE POTENTIALS; O-XYLENE FRAGMENT; MOLECULAR CALCULATIONS; REDOX PROPERTIES; FUSED PORPHYRIN; COMPLEXES; ISOMER; TETRAPHENYLPORPHYRIN; TETRAARYLPORPHYRINS; BISPORPHYRINS;

D O I：

10.1002/ejoc.200900338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid-catalyzed exocyclic ring formation in meso-tetrakis(3',5'-dimethoxyphenyl)-2-aza-21-carbaporphyrin takes place regioselectively between the external carbon atom of the confused pyrrole and the ortho-carbon atom of the adjacent meso-aryl group. The ring fusion strongly alters the spectroscopic properties of the macrocycle, but its aromaticity is preserved, as shown by NMR spectroscopy as well as DFT calculations. A tendency to self-associate is observed for partially protonated and nickel (II)-metalated systems. A novel silver(I)-bridged dimer is formed in the reaction of the fused carbaporphyrin with AgBF4. Cyclic voltammetry studies of this system indicate an interaction between the subunits. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3930 / 3939

页数：10

共 47 条

[41]

2-8

[42]

Tsuda A, 2000, ANGEW CHEM INT EDIT, V39, P558, DOI 10.1002/(SICI)1521-3773(20000204)39:3<558::AID-ANIE558>3.0.CO

[43]

2-G

[44] Cruciform porphyrin pentamers [J].

Vicente, MGH ;

Cancilla, MT ;

Lebrilla, CB ;

Smith, KM .

CHEMICAL COMMUNICATIONS, 1998, (21) :2355-2356

[45] ABINITIO EFFECTIVE CORE POTENTIALS FOR MOLECULAR CALCULATIONS - POTENTIALS FOR MAIN GROUP ELEMENTS NA TO BI [J].

WADT, WR ;

HAY, PJ .

JOURNAL OF CHEMICAL PHYSICS, 1985, 82 (01) :284-298

[46] EFFICIENT IMPLEMENTATION OF THE GAUGE-INDEPENDENT ATOMIC ORBITAL METHOD FOR NMR CHEMICAL-SHIFT CALCULATIONS [J].

WOLINSKI, K ;

HINTON, JF ;

PULAY, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8251-8260

[47] Diels-Alder reactions of nickel(II) N-confused porphyrins as dienophiles [J].

Xiao, ZW ;

Patrick, BO ;

Dolphin, D .

CHEMICAL COMMUNICATIONS, 2002, (17) :1816-1817

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